2C-T

2C-T, or 2C-T-1, also known as 4-methylthio-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.^[1][2] It is taken orally.^[1] The drug has a relatively short duration and is of relatively low potency among the 2C psychedelics.^[1]

2C-T

Clinical data
Other names	2C-T-1; 4-Methylthio-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-methylthiophenethylamine
Routes of administration	Oral[1]
Drug class	Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Legal status
Legal status	In general unscheduled
Pharmacokinetic data
Onset of action	15 minutes[1]
Duration of action	3–5 hours[1]
Identifiers
IUPAC name 2-[2,5-dimethoxy-4-(methylsulfanyl)phenyl]ethan-1-amine
CAS Number	61638-09-3 N
PubChem CID	12315927
ChemSpider	10438674 Y
UNII	E5X0VFF7S4
ChEMBL	ChEMBL127252 Y
CompTox Dashboard (EPA)	DTXSID60487530
ECHA InfoCard	100.215.648
Chemical and physical data
Formula	C11H17NO2S
Molar mass	227.32 g·mol−1
3D model (JSmol)	Interactive image
SMILES CSc1cc(OC)c(cc1OC)CCN
InChI InChI=1S/C11H17NO2S/c1-13-9-7-11(15-3)10(14-2)6-8(9)4-5-12/h6-7H,4-5,12H2,1-3H3 Y Key:UPZMYCMLLQTYEM-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

The drug acts as an agonist of the serotonin 5-HT₂ receptors, including of the serotonin 5-HT_2A receptor.^[3] It is the parent compound of the 2C-T series of psychedelic phenethylamines, with derivatives such as 2C-T-2, 2C-T-4, 2C-T-7, and 2C-T-21, among many others.^[1][2]

2C-T was first described in the scientific literature by David E. Nichols and Alexander Shulgin in 1976.^[4][2] It was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).^[1][2]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists 2C-T's dose range as 60 to 100 mg orally and its duration as 3 to 5 hours.^[1] Its onset is described as 15 minutes and its effects are said to develop "very quickly but very quietly".^[1] It is one of the shortest-acting of the 2C psychedelics as well as among the least potent.^[1]

The effects of 2C-T have been reported to include being "really psychedelic", little or nothing in the way of psychedelic visuals, some fantasy with music, increased appreciation of poetry, things feeling "opened up" like with MDMA, being a possible MDMA substitute in this regard, feeling somewhat "generic" as a psychedelic, intellectual thinking overpowering emotions, conversational facilitation, tactile enhancement, enhanced eroticism, and stomach discomfort.^[1]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

2C-T shows affinity for the serotonin 5-HT₂ receptors and is known to act as an agonist of the serotonin 5-HT_2A and 5-HT_2B receptors.^[3] The drug shows no affinity for the monoamine transporters.^[3]

Chemistry

2C-T is in a class of compounds commonly known as phenethylamines, and is the 4-methylthio analogue of 2C-O, a positional isomer of mescaline. It is also the 2C analog of Aleph. The systematic name of the chemical is 2-(2,5-dimethoxy-4-(methylthio)phenyl)ethanamine. The CAS number of 2C-T is 61638-09-3.

Synthesis

The chemical synthesis of 2C-T has been described.^[1][2]

Derivatives

A large number of derivatives of 2C-T have been developed and described.^[1] These include 2C-T-2, 2C-T-3, 2C-T-4, 2C-T-7, 2C-T-21, and CYB-210010 (2C-T-TFM or 2C-T-36), among many others.^[1]

History

2C-T was first synthesized and studied through a collaboration between David E. Nichols and Alexander Shulgin.^[4] It was first described in the scientific literature in 1976.^[4]

Society and culture

Legal status

Canada

As of October 31, 2016; 2C-T is a controlled substance (Schedule III) in Canada.^[5]

United States

2C-T is unscheduled and unregulated in the United States; however its close similarity in structure and effects to 2C-T-7 could potentially subject possession and sale of 2C-T to prosecution under the Federal Analog Act. This seems to be the tack the federal government is taking in the wake of the DEA's Operation Web Tryp. A series of court cases in the US involving the prosecution of several online vendors were commenced in 2004 and resulted in a number of convictions.^[6]

See also

• 2C (psychedelics)
• Substituted methoxyphenethylamine